Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5228547 | Tetrahedron | 2008 | 10 Pages |
Abstract
We describe an intriguing new example of a parallel kinetic resolution; an asymmetric cyclization-carbonylation of propargyl ketols catalyzed by palladium(II) with chiral bisoxazoline (box) ligands. The 2S,3S enantiomer of (±)-6 was preferentially converted to 13 (45-49% yields, 37-46% ee), and the 2R,3R enantiomer of (±)-6 was preferentially converted to 14 (21-23% yields, 92-97% ee). As an application of this reaction, formal synthesis of (+)-bakkenolide A was achieved.
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Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Keisuke Kato, Satoshi Motodate, Satoshi Takaishi, Taichi Kusakabe, Hiroyuki Akita,